The Style-Conscious Jet Setter
Blend in with the locals while you hit sidewalk cafés, museums, and boutiques—then roll your finds home in a trolley that never ceases to be chic.
Prada leather suitcase, $2,995, at Prada, 30 E. Oak St.; 312-951-1113, prada.com.
3 MUST-BRINGS
Parisian Chic: A Style Guide book by Ines de la Fressange, $30, at borders.com.
Leica D-Lux 5 digital camera, $799, at Central Camera Company, 230 S. Wabash Ave.; 312-427-5580, centralcamera.com.
Hermès cashmere and silk shawl, $1,075, at Hermès, 25 E. Oak St.; 312-787-8175, hermes.com.
Photography: Courtesy of vendors
The Frequent Flier
Go beyond suits and ties with an expandable bag that makes space for board shorts, casual button-downs, and other after-hours essentials.
Hideo Wakamatsu tarpaulin carryon, $225, at Flight 001, 1133 N. State St.; 312-944-1001, flight001.com.
3 MUST-BRINGS
Jack Spade printed bill holder, $145, at Jack Spade, 47 E. Oak St.; 312-915-0315, jackspade.com.
Steven Alan baseball cap in purple houndstooth, $120, at stevenalan.com.
WANT Les Essentiels de la Vie leather iPad case, $295, at Barneys New York, 15 E. Oak St.; 312-587-1700, barneys.com.
Photography: Courtesy of vendors
The Cool-Hunting Traveler
Can’t-miss colors trim minutes at the baggage claim—and free up more time for gallery-hopping (or relaxing by the pool).
Tumi expandable carryon, $595, at openingceremony.us.
4 MUST-BRINGS
Works on Whatever Ed Ruscha towel, $95, at worksonwhatever.com.
Timex 80 watch, $55, at RSVP Gallery, 1753 N. Damen Ave.; 773-770-6666, rsvpgallery.com.
Postalco notebook, $35, at Space519, 900 N. Michigan Ave., Level 5; 312-751-1519, space519.com.
Caran d’Ache ballpoint pen, $18, at goldspot.com.
Photography: Courtesy of vendors
The Eco-Adventurer
Torrents of rain can’t stop your trek when this waterproof duffel—which doubles as a backpack—is protecting your gear.
Patagonia water-resistant polyester duffel, $129, at Patagonia, 1800 N. Clybourn Ave.; 312-951-0518, patagonia.com.
3 MUST-BRINGS
Sierra Designs poncho, $30, at sierradesigns.com.
Lifekind organic travel pillow, $59, at lifekind.com.
Katadyn water bottle with purifier, $50, at REI, 17W160 22nd St., Oakbrook Terrace; 630-574-7700, rei.com.
Photography: Courtesy of vendors
The Romantic Weekenders
A classic carrier with two compartments is the ideal size for making a quick retreat. Stash mood-setting music, bubbly, and a gourmet spread. After that? Love is all you’ll need.
Filson twill shoulder bag, $370, at filson.com.
3 MUST-BRINGS
Altec Lansing speaker system, $130, at alteclansing.com.
2004 Vilmart Grand Cellier d’Or Champagne, $85, at Binny’s, 213 W. Grand Ave.; 312-332-0012, binnys.com.
Bed Bath & Beyond 21-piece insulated picnic basket, $40, at bedbathandbeyond.com.
Photography: Courtesy of vendors
The Bohemian Beachcomber
Effortlessly shift from shoreside cabana to nightclub with a lineup of mix-and-match basics tucked into an offbeat (yet luxe) tote.
Vanessa Bruno sequin-embellished leather duffel, $649, at lagarconne.com.
3 MUST-BRINGS
Marc Jacobs round-frame sunglasses, $295, at Marc Jacobs, 11 E. Walton St.; 312-649-7260, marcjacobs.com.
Calypso St. Barth silk scarf, $250, 50 E. Oak St.; 312-649-9934, calypsostbarth.com.
Newbark canvas flats, $210, at net-a-porter.com.
Photography: Courtesy of vendors